25518-51-8
Chemical Structure
(+)-Decanoylcarnitine
- CAS No.: 25518-51-8
- Formula:C17H33NO4
- Molecular Weight:315.45
IUPAC Name: (S)-3-(decanoyloxy)-4-(trimethylammonio)butanoate
InChIKey: LZOSYCMHQXPBFU-HNNXBMFYSA-N
SMILES: [C@@H](OC(CCCCCCCCC)=O)(C[N+](C)(C)C)CC([O-])=O
Biological Activity: (+)-Decanoylcarnitine is an (S)-acylcarnitine derivative and a potent inhibitor of carnitine-acylcarnitine translocase, with an IC50 of 5 μM. (+)-Decanoylcarnitine acts as a competitive inhibitor of long-chain acylcarnitine transferase and (-)-carnitine palmityltransferase. (+)-Decanoylcarnitine blocks hepatic fatty acid oxidation, ketogenesis, oleate-induced activation of gluconeogenesis, as well as associated changes in acetyl-CoA, citrate, redox pair ratios, flavins and pyridine nucleotides. (+)-Decanoylcarnitine reverses ketosis in vivo, enhances insulin-mediated hypoglycemic effects in anesthetized animals, and reduces plasma ketone body levels when used in combination with insulin. (+)-Decanoylcarnitine can be used in studies related to diabetic ketoacidosis[1][2][3].
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(+)-Decanoylcarnitine | (+)-Decanoylcarnitine is an (S)-acylcarnitine derivative and a potent inhibitor of carnitine-acylcarnitine translocase, with an IC50 of 5 μM. (+)-Decanoylcarnitine acts as a competitive inhibitor of long-chain acylcarnitine transferase and (-)-carnitine palmityltransferase. (+)-Decanoylcarnitine blocks hepatic fatty acid oxidation, ketogenesis, oleate-induced activation of gluconeogenesis, as well as associated changes in acetyl-CoA, citrate, redox pair ratios, flavins and pyridine nucleotides. (+)-Decanoylcarnitine reverses ketosis in vivo, enhances insulin-mediated hypoglycemic effects in anesthetized animals, and reduces plasma ketone body levels when used in combination with insulin. (+)-Decanoylcarnitine can be used in studies related to diabetic ketoacidosis. | |||||||||||||||||||||
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References
- [1]. McGarry JD, et al. Acute reversal of experimental diabetic ketoacidosis in the rat with (+)-decanoylcarnitine. The Journal of clinical investigation. 1973 Apr;52(4):877-84. [Content Brief]
- [2]. Williamson JR, et al. Inhibition of Fatty Acid Stimulation of Gluconeogenesis by (+)-Decanoylcarnitine in Perfused Rat Liver. Diabetes. 1968;17(4):194-208.4
- [3]. Ceccarelli SM, et al. Carnitine palmitoyltransferase (CPT) modulators: a medicinal chemistry perspective on 35 years of research. Journal of Medicinal Chemistry. 2011;54(9):3109-3152.
